Real stories about dating and relationships in New York City. Truth is more interesting than fiction.

It’s a Small World

Its a Small World batshit crazy  1217438 44565512 230x300I was on a date. A . With a guy I met online. From the moment we met, he looked vaguely familiar. Not from his photos, but as if we’d met before. He looked like his photos. But he didn’t seem familiar in the photos. Go figure.

It hit me about 15 minutes in. After we’d been talking for a while and I heard more about his life, background, etc. He said something that made it all click. We’d met before. More than that. We were casual acquaintances from over 15 years earlier. But there was no way in I was going to say anything about it to him.

Way back in my mid 20s, he was dating a friend of mine. Needless to say, we were both very different people then.

I don’t want to get into the nitty-gritty, but let’s just say he wasn’t a good guy back then. NOT. A. GOOD. GUY. In fact, last I’d heard of him, he’d gone into rehab, left and then disappeared. Or something like that.

Anyway, so there we were on our date. Our first date. And I’m 99.99999% sure that this is the same guy. But I didn’t feel comfortable asking him about it. Because, well, who wants to be reminded of what was probably the very worst time in their life, years later?  He was presenting himself as a totally different guy, now.

Successful. With his shit together.

It would have been rude of me, at the very least, to ask him about his ugly past.

So I didn’t.

We also didn’t have a . Even though he asked. For a few reasons, but mainly because I couldn’t get past my very unpleasant memories of who he used to be. It would have been different if he had disclosed that he had past issues with addiction. Which he didn’t. Or if he wasn’t drinking on our date. Which he WAS.

This happened last year, and I still think of it and him, occasionally. I wonder if I did the right thing. Maybe I should have said something? Maybe I should have gone out with him again, and said something on the next date?  Or maybe I was smart to walk away when I did.


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11 to “It’s a Small World”


  1. matt says:

    Why would he disclose to you anything bad about his past on the first date?

    Had he told you about his past and all the bad things he had done, you probably wouldn’t have went out with him again anyway.

    People do change. I feel like this was unfair of you to judge him so harshly.

    Don’t want this comment to come off mean, love your blog and usually I agree with your posts but I have strong feelings about this one.

    • Simone Grant says:

      You’re not coming off as mean, at all. And I don’t disagree with you. If someone asked me if they should mention a history of addiction on the first date, I’d probably say no.

      BUT, he was drinking. And I knew about his history. Which made me feel really uncomfortable. Maybe I misjudged him. There are people who are able to battle their demons, and drink responsibly, years after rehab etc. But it made me uncomfortable. And I couldn’t unknow what I knew.

      I’m not saying I was right. But it’s how I felt.

  2. Paul says:

    Probably best to trust your gut in a situation like that.

    BTW – What happened to the radio show? I enjoyed it!

    • Simone Grant says:

      Thanks so much for asking. Honestly, we (Sherri and I) were both overcommitted. And we decided we had to let something go. The Radio Show was non-essential.

      Hopefully I’ll find a time to do something like that in the future. It was fun.

  3. Although it’s tempting to give second chances, Its hard for anyone to change permanently. Addiction is a life long battle and you would have to deal with this forever.

  4. Chiara says:

    What a fun situation! I would have said something.. And here’s why:
    A lot can change in 15 years. In fact, from your mid 20′s on things SHOULD change! Bringing it up wouldn’t have necessarily been a bad idea.. If he really did get his shit together he probably wouldn’t have been uncomfortable talking about the person he used to be.

    But wow, what a small world!

  5. cougel says:

    Very interesting question. Personally, I believe that if there is something there and you would go out with him again (had you not known him in the past), then you should. It’s not so much that people do change but that your pov of the situation (via your friend) so many years ago has a whole other side to it. Think about the things you might have done that to others seemed awful…you never know what his story was then, or what it is now.

  6. Jen says:

    I think you did the right thing. People dont change….people CAN change but people dont change….Sounds like a contradition…it is not. All people are capable of change. They have to want it, work for it, strive for it everyday…. When someone says “people change”…nope, not be magic or by accident or even through growing older…not unless they really strive for it.

    Does time alter us…sure…slightly alter us. Someone brash and obnoxious, may become assertive and feisty…but they’ll never magically becoming a shrinking violet, shy wallflower. Now, if they try to become this for some reason, then sure they could.

    So, if your date with the past drinking problem is sitting there with a drink in his hand but a good job…the good job is more of the “people change via time route”…whereas drinking or not drinking (when you know he had a problem) is indicative of him “trying or not trying” to change.

    just my two cents…and at the end of the day, always trust your instincts.